(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-2H5)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-one

• ChemBase ID: 160638
• Molecular Formular: C19H30O2
• Molecular Mass: 290.4403
• Monoisotopic Mass: 290.2245802
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)C)O
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1
• InChIKey: QGXBDMJGAMFCBF-BNSUEQOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-one
• IUPAC Traditional name: (1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-one
• Synonyms: (3α,5β)-3-Hydroxyandrostan-17-one-d5; 3α-Hydroxy-5β-androstan-17-one-d5; 3α-Etiocholanolone-d5; 3α-Hydroxy-5β-androstane-17-one-d4; 5-Isoandrosterone-d5; 5β-Androstan-3α-ol-17-one-d5; 5β-Androstane-3α-ol-17-one-d5; Aetiocholanolone-d5; Etiocholan-3α-ol-17-one-d5; Etiocholanolone-d5; NSC 50908-d5; α-Etiocholanolone-d5; 5β-Androsterone-d5

Database IDs

• PubChem SID: 162254773
• PubChem CID: 71313408

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.7672846
• LogD (pH = 7.4): 3.7672846
• Log P: 3.7672846
• Molar Refractivity: 83.8089 cm^3
• Polarizability: 33.49998 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A637632

Labelled 5β-Androsterone (A637630). 5β-Androsterone is a metabolite of Testosterone (T155000). 5β-Androsterone is a stereoisomer of Androsterone (A637535). 5β-Androsterone showed a weak estrogenic action.

REFERENCES

• Park, J., et al.: J. Anal. Toxicol., 14, 66 (1990)
• Palonek, E., et al.: J. Steroid Mol. Biol., 55, 121 (1990)
• Aguilera, R., et al.: Clin. Chem. 47, 292 (1990)
• Flenker, U., et al.: Steroids, 73, 408 (1990)